[(1R,2S,5R,7S,9S,11R,12R,15S,17S,18S,19S)-2-acetyloxy-12,15-dihydroxy-9-(4-hydroxyphenyl)-17-(2-hydroxypropan-2-yl)-14,19-dimethyl-4,8,10-trioxapentacyclo[9.7.1.02,5.07,19.013,17]nonadec-13-en-18-yl] (E)-2-methylbut-2-enoate

Details

• Internal ID: 8c157116-3fca-4f7c-9aec-add50e03aa6f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(1R,2S,5R,7S,9S,11R,12R,15S,17S,18S,19S)-2-acetyloxy-12,15-dihydroxy-9-(4-hydroxyphenyl)-17-(2-hydroxypropan-2-yl)-14,19-dimethyl-4,8,10-trioxapentacyclo[9.7.1.02,5.07,19.013,17]nonadec-13-en-18-yl] (E)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C2C3(C(CC4C2(CO4)OC(=O)C)OC(OC3C(C5=C(C(CC15C(C)(C)O)O)C)O)C6=CC=C(C=C6)O)C
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@H]1[C@H]2[C@]3([C@H](C[C@@H]4[C@]2(CO4)OC(=O)C)O[C@@H](O[C@H]3[C@@H](C5=C([C@H](C[C@@]15C(C)(C)O)O)C)O)C6=CC=C(C=C6)O)C
• InChI: InChI=1S/C34H44O11/c1-8-16(2)29(39)43-28-26-32(7)22(13-23-34(26,15-41-23)45-18(4)35)42-30(19-9-11-20(36)12-10-19)44-27(32)25(38)24-17(3)21(37)14-33(24,28)31(5,6)40/h8-12,21-23,25-28,30,36-38,40H,13-15H2,1-7H3/b16-8+/t21-,22-,23+,25+,26-,27-,28-,30-,32+,33-,34-/m0/s1
• InChI Key: VCWXYABBLLDDKF-XALFMGAJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₄O₁₁
• Molecular Weight: 628.70 g/mol
• Exact Mass: 628.28836222 g/mol
• Topological Polar Surface Area (TPSA): 161.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 2.99
• H-Bond Acceptor: 11
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9820	98.20%
Caco-2	-	0.8079	80.79%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7893	78.93%
OATP2B1 inhibitior	-	0.8573	85.73%
OATP1B1 inhibitior	+	0.8191	81.91%
OATP1B3 inhibitior	+	0.9096	90.96%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9593	95.93%
P-glycoprotein inhibitior	+	0.7437	74.37%
P-glycoprotein substrate	+	0.7243	72.43%
CYP3A4 substrate	+	0.7185	71.85%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8917	89.17%
CYP3A4 inhibition	-	0.6785	67.85%
CYP2C9 inhibition	-	0.6568	65.68%
CYP2C19 inhibition	-	0.7269	72.69%
CYP2D6 inhibition	-	0.8959	89.59%
CYP1A2 inhibition	-	0.7617	76.17%
CYP2C8 inhibition	+	0.8090	80.90%
CYP inhibitory promiscuity	-	0.8285	82.85%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4602	46.02%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.9024	90.24%
Skin irritation	-	0.6899	68.99%
Skin corrosion	-	0.9261	92.61%
Ames mutagenesis	-	0.5502	55.02%
Human Ether-a-go-go-Related Gene inhibition	+	0.8105	81.05%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	+	0.5795	57.95%
skin sensitisation	-	0.8122	81.22%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.8323	83.23%
Acute Oral Toxicity (c)	I	0.4381	43.81%
Estrogen receptor binding	+	0.8195	81.95%
Androgen receptor binding	+	0.7413	74.13%
Thyroid receptor binding	+	0.6143	61.43%
Glucocorticoid receptor binding	+	0.7625	76.25%
Aromatase binding	+	0.7469	74.69%
PPAR gamma	+	0.7227	72.27%
Honey bee toxicity	-	0.6066	60.66%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6900	69.00%
Fish aquatic toxicity	+	0.9925	99.25%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.39%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.14%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.14%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.29%	97.09%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	94.32%	90.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.21%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.58%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.63%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.62%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	89.90%	94.73%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.23%	97.14%
CHEMBL284	P27487	Dipeptidyl peptidase IV	86.21%	95.69%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.98%	97.28%
CHEMBL340	P08684	Cytochrome P450 3A4	84.85%	91.19%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	84.38%	85.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.03%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.52%	95.89%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.34%	96.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.98%	99.23%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.54%	100.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.43%	94.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.22%	99.17%

Plants that contains it

• Equisetum hyemale

Cross-Links

• PubChem: 44233386
• NPASS: NPC268560